What DailyWorth’s Founder Taught Me About Money

February 11, 2016

Connect Member

Founder of Hilary Hendershott Financial. Empowering one million women to become millionaires.


In a world of empty marketing-speak and lip service from companies that want to “make a difference” and “leave a legacy,” Amanda Steinberg has truly found a way to marry good intentions with powerful results. Amanda created DailyWorth as a place for women to gather and find support. It’s a place where we can move past our financial limits. Personally, I can vouch that she inspired me to move past my self-imposed limits.

I had been mulling over the concept behind my podcast, Profit Boss Radio, for more than a year. I imagined a place where women could tune in anytime to hear inspiring and well-respected women get real about money. I wanted these women to share in a conversation that is still unfortunately taboo in most circles.

But I was afraid. Consequently, I didn’t pull the trigger.

Then, in August of last year, Amanda announced a Twitter discussion on women and money. I hopped onto the Twitter chat. I awkwardly posed a question to Amanda about her financial plans, clearly revealing myself as a terrible tweeter!

Her response terrified me, but I took the leap.

Hilary: Amanda, what do you envision for your own (financial/retirement) future? How do you think about your position as a role model?

Amanda: Girl, I need need more than 140 characters for those Qs! :-)

Hilary: :) I have just the forum for you. Be my guest on the Million Millionaires Podcast (coming soon). You’re a hot topic!

Amanda: FUN! and done.

And voilà!

I certainly wasn’t going to miss this opportunity. I did a little market research, upgraded the podcast’s name from The Million Millionaires Podcast to Profit Boss Radio, and a show was born! It was only appropriate that, when the show launched in the first week of February, Amanda’s long-awaited interview got top billing.

Here are three great things I learned from my hour-long chat with DailyWorth’s CEO:

1. You can’t tell what someone’s financial life is like from the outside.
I admit that when I saw this photo of Amanda in Cosmopolitan wearing $300 pants and a $245 blouse, I wasn’t sure about her relatability.

But Amanda readily admits she’d been too financially freewheeling in her former life as a highly-compensated computer programmer. She soon found herself with both a sprawling home and sticker shock over the unexpected tax bills and necessary home improvement projects.

Amanda was at a crisis point that led her to a personal growth workshop, where she discovered that the stories she had grown up telling herself about money had codified her money life. The moment she discovered she could save herself, Amanda envisioned a place where other women could come when they also realized it was time to escape the negative money beliefs of their past.

The seeds for DailyWorth had been planted.

I, too, can vouch for the fact that when it comes to people’s money, things are often not what they seem. After all, in my 15 years as a financial advisor for women, I’ve been privy to the inner workings of hundreds of affluent clients’ financial lives.

Typically, the women with few financial worries aren’t succumbing to the pressure of creating a life that makes them look good to others. In my office, I rarely see women dripping in pearls and country club memberships. Instead, my happiest and wealthiest clients are financially conservative. These clients know what they can spend to preserve their wealth. They also only pay for the things and experiences that make them the happiest.

So, what does this mean for you? It means that you can stop comparing your life to what you think other people’s lives are like. Like, stop it now.

That friend of yours who drives the Mercedes SL? It doesn’t mean she’s debt-free and rolling in dough. In fact, chances are she gave up some financial freedoms to get her hands on a car that makes her look … well, financially free.  

Comparisons always hurt and never help. Even if you come out on top of the comparison, the win is empty.

2. It’s okay to think about your financial future in non-traditional ways.
Amanda shared that she and her long-term romantic partner keep not only separate finances, but also separate homes. This isn’t for reasons of Victorian modesty; it’s what works for them.  

We also talked specifically about her retirement savings goal. I like to call it your “economic independence” number. Surprisingly, even though she’s a powerful CEO with VC connections and media galore, she says she isn’t 100 percent sure that she’ll achieve it. Amanda encourages us to be flexible in our thinking, and not to think of retirement goals in terms of “winning” or “losing.”

Now that’s a pretty revolutionary way of thinking, especially when you consider that DailyWorth’s offices are a stone’s throw from Wall Street — and Wall Street embodies the concept of the zero-sum game.

For more on how Amanda navigates finances and romance, as well as retirement goal specifics, listen to the episode.

3. The money story you tell about yourself matters.
In her turnaround moment, Amanda discovered that she had spent a lifetime telling herself she was a spender. She thought she was describing what already was, but her words were a creative act.

In my TEDx talk, I shared that in my money story, there was never enough money. Life gave me a fat paycheck anyway, so to make my story true (which is all your brain knows how to do), I spent it all and then some.

What money stories are you telling about yourself today?

You have years of experience telling that story, so you’ll have lots of evidence that it’s true. But is it empowering? Do you like the results you’re living in?

If not, you have the power to rewrite your story and save yourself.

To transform your money story in a supportive and compassionate environment, check out my interview with Amanda Steinberg, and consider subscribing to Profit Boss Radio today.

Hilary Hendershott is a member of the DailyWorth Connect program. Read more about the program here.